


Feeling Cocky

by YlvaUllsdotter



Category: Supernatural
Genre: 18+, Anal Fingering, Cocky!Dean, Dean Winchester - Freeform, Dean x Reader, Established Relationship, F/M, Fanfiction, Fanfiction Cockyweek, Gag, NSFW, One-Shot, Panty Gag, Reader Insert, SPN - Freeform, Sexual role play, Smut, Sub!Dean, Supernatural - Freeform, blowjob, domme!Reader, gagged, oral sex (male receiving), panties as gag, reader - Freeform, role play
Language: English
Status: Completed
Published: 2018-05-21
Updated: 2018-05-21
Packaged: 2019-05-09 21:20:27
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,878
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14723789
Author URL: https://archiveofourown.org/users/YlvaUllsdotter/pseuds/YlvaUllsdotter
Summary: Dean's cocky smirk makes you want to show him who's boss.





	Feeling Cocky

**Author's Note:**

> Written for Fanfiction Cocky Week. I can’t stand bullies. Mind the tags. I apologize for nothing.

She was used to being hit on by drunk guys. After all, that was one of the ‘perks’ of being a female bartender. A little harmless flirting got her bigger tips, and she had become quite adept at turning them down without causing any hard feelings. 

This guy though, he was something else. She could tell that he had the potential to be dangerous, despite his delicate features, and she had always had a soft spot for bad boys. In between serving drinks and cleaning up, she found herself studying him. The way his fingers wrapped around the tumbler of amber liquid. The way his lips pressed against the edge of the glass. The way his tongue would slip out and collect a stray drop from his lips. 

A couple of times, he caught her looking and flashed a cocky grin at her as if he knew perfectly well what kind of effect he was having on her. When her replacement arrived, she stayed behind the bar for a bit, both to help out and to have the counter between them when she approached the guy. 

“Another?” Her voice was hoarse from having to communicate with the bar patrons over the sound of the music. 

He looked up and downed the last sip from his glass before sliding it over to her, flashing her another cocky grin. “Sure, sweetheart. Hit me.”

She tipped the bottle of Jack Daniel’s, the whiskey pouring into the tumbler, then slid the glass back across the counter. Grabbing a clean glass, she poured a drink for herself as well before setting the bottle down. He raised an eyebrow, smirking knowingly at her.

“Drinking on the job?”

She shrugged and took a sip of the whiskey. “Technically, I’m off,” she replied, her eyes on his. She noticed they were the most intense green she had ever seen. 

“So you decided to share a drink with me? I’m flattered,” his green eyes sparkled at her. 

“Yeah, well, you’ve been checking me out all night, I figured I might as well get your name,” she shot back. His cocky attitude was starting to get to her and she had the urge to take him down a peg.

“Oh. Well, I’m Dean,” he held his hand out across the counter, that smirk still firmly in place.

She slipped her slender fingers in his, giving his hand a firm squeeze. His smirk faltered just the slightest bit at feeling her strong grip.

“Y/N.” She kept her tone neutral, not wanting to give him any more than she had to.

“Nice to meet you, Y/N. And yeah, you’re right, I have been checking you out all night. I couldn’t help myself, you are the prettiest girl in the place.” He winked at her. Actually winked. She had made up her mind at that moment. Returning his smile, she put on a coy expression, looking at him through her eyelashes as she took another sip of her drink.

“That’s so sweet. You ain’t so bad yourself,” she flirted back, feeding his cockiness.

“Well, since you’re off now, what do you say you and I get outta here? Go someplace more private?” His tone told her he was certain she would say yes and she gave a mental snort at his attitude. 

“I’d love to,” was all she said out loud, though. Finishing her drink, she picked up her tips and her jacket and met Dean outside the entrance. He slipped an arm around her waist as he led her to his car, a gorgeous classic Chevy Impala that almost made up for his attitude. 

When he led her around the car to the passenger side, he pressed her back against the door, his hands coming up to rest on her hips as he moved into her space. She had to mentally restrain herself to not take control when his lips met hers and his hands slowly slid up her sides. Instead, she wrapped her arms around his neck and returned the kiss, reluctantly admitting to herself that those plump lips of his felt good against hers. The man knew how to kiss, for sure.

They were both breathing hard when he pulled away, that infuriatingly cocky smirk back on his face as he opened the door for her. She slid onto the bench seat and took a few moments to collect her thoughts while Dean rounded the hood of the car and got into the driver’s seat. 

The rumble of the engine was somehow soothing, thankfully, since neither of them said anything during the short drive. He pulled in at the motel down the road, parking in front of one of the rooms. Once they were inside, he pushed her up against the closed door, crushing his lips to hers, his hands sliding up her body, stopping to caress her breasts through her tank top for a few moments before moving on to slip the leather jacket off her shoulders. She let the jacket fall to the floor, wrapping her arms around his shoulders and returning the kiss. Without much effort, she turned them around so that his back was pressed against the door. When his lips parted on a moan, her tongue slipped between them to claim his mouth. Their tongues wrestled for dominance for a short moment before he gave in and let her take control. 

With deft hands she quickly got his top layers off, letting her hands explore the expanse of freckled skin. His hands had come to rest on her hips, pressing her against him, and she felt his cock stiffen and twitch against her when she twisted his nipples between her fingers. The moan he let out was muffled by her lips on his, but it went straight to her core.

She moved away long enough to unbuckle his belt and let him slip his jeans off before pushing him towards the bed. He stumbled slightly, but easily kept his balance, impressing her with his dexterity. He watched her with anticipation, that cocky little smirk creeping back to his face while she pulled her tank top over her head and unzipped her denim skirt. Leaving the clothes in a pile on the floor, she stalked towards him, almost as tall as he was in the strappy heels she was still wearing.

He swallowed hard as his eyes took her in, naked but for a matching set of black lace lingerie and those heels. Before he had time to say anything, she gave him a shove and he landed on his back on the bed, the cockiness replaced by eager anticipation. She reached behind her and undid her bra, letting it slip off her arms, then slipped out of her panties. Picking the panties up, she straddled his legs and crawled up his body. With one hand she gripped his face, her lips brushing against his just enough to make him part his. Quick as a snake, her other hand came up and stuffed her panties in his mouth.

“That should keep you quiet,” she purred at him, her eyes taking on a wicked gleam in the low light of the motel room. She grabbed his wrists, easily holding him down while she lowered her pulsing cunt to slide over his cock, trapping it between them. “You’ve got quite the cocky attitude, Dean. I don’t like it. So tonight, you’re gonna shut up and take it, like a good boy, while I have my way with you.” While she spoke, she slid her slick folds over his cock, rubbing her clit against him and rolling her hips, drawing muffled moans from his stuffed mouth.

He tried to buck his hips up against her, but her weight held him down while she kept grinding her pussy on his throbbing cock at her own pace. Letting go of his wrists, her hands went to her breasts, cupping them and rolling the nipples in her fingers. She looked down at him through half-lidded eyes, enjoying the look of utter debauchery. It looked so much better on him than the cocky smirk.

One hand slid down her body to rub circles over her clit, and with a sharp cry, she reached her climax, her juices coating his length where it was still trapped against her cunt. She stayed there on top of him while the aftershocks rippled through her.

Once she had come down from her high, she smirked down at him. Leaning down, she ran the tip of her tongue over his lips, soothing the discomfort of being stretched by the panties stuffed in his mouth. Her lips nipped along his jawline and down the column of his throat, stopping at the juncture where his neck met his shoulder to suck hard, leaving a dark bruise, before moving on. She kissed along his clavicle, then down to his nipple, taking it between her teeth. Looking up at him through her lashes, she saw him watching her as she bit down on the nipple. His muffled groan made her pussy throb. She shifted above him to repeat her action on his other nipple, drawing another muffled groan from him. 

Almost regretting gagging him, she moved down his body until she had his cock right in front of her. While he watched, she wrapped her fingers around the slick length and stroked him slowly. The breaths coming through his nose were heavy and ragged, and when she bent down and took his cock into her mouth, his head fell back against the pillow and he cried out.

Watching him the whole time, she sucked hard on just the tip, her tongue swirling over the velvety skin. She alternated between licking his slit and swiping her tongue over his sweet spot, just below the head. Within moments he was trembling with need, his hips thrusting unconsciously as he sought the friction to reach his release. She slipped one hand between his legs, coating a finger in the mixture of her saliva, her pussy juices, and his pre-come that had dribbled down his shaft. At the same time as she sucked him further into her mouth, she slipped her finger into his ass, drawing another cry of pleasure from him. 

Panting hard and emitting a string of muffled sounds, he reached his climax, shooting his load in her warm wet mouth. She watched him through it all, reveling in the sight of him all strung out with pleasure. 

When he finally relaxed, she carefully pulled the soaked panties from his mouth. After cleaning him up, she grabbed a bottle of water out of the mini-fridge and helped him drink some. When a few drops dribbled down his chin, she caught them with her tongue before placing a soft kiss on his lips. Setting the bottle on the nightstand, she snuggled up next to him, her head on his chest, listening to the sound of his heart. The thumping was drowned out by the rumble when he spoke.

“How did you get the bartender to let you work the bar, anyway?” His voice was tired and amused.

“I paid him a lot of money,” she grinned against him.

He chuckled and his arm around her waist squeezed her, pulling her closer.


End file.
